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Preparation of Bis(beta-Trimethylsilylethanesulfonyl)imide and Its Use in the Synthesis of Protected Amine Derivatives

Preparation of Bis(beta-Trimethylsilylethanesulfonyl)imide and Its Use in the Synthesis of Protected Amine Derivatives

David M Dastrup, Michael P VanBrunt, Steven M Weinreb

J Org Chem. 2003 May 16;68(10):4112-5.

PMID: 12737604

Abstract:

Bis(beta-trimethylsilylethanesulfonyl)imide (SES(2)NH) can be easily prepared in 85% yield by alkylation of the trianion of bismethanesulfonimide with 2 equiv of commerically available (iodomethyl)trimethylsilane. This synthon undergoes effective Mitsunobu alkylation reactions with both primary and secondary alcohols to afford the corresponding bis-SES imides. These imides can be selectively cleaved to the mono-SES-protected amines, and in addition undergo a one-pot cleavage/N-alkylation to afford SES derivatives of secondary amines.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4206671	(Iodomethyl)trimethylsilane		4206-67-1	Price

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